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$128+ Cheap flights from Indiana to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
IND — YWG
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Indiana to Winnipeg

Cheapest flights from Indiana to Winnipeg
Explore the most affordable flight options available from Indiana to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This oojo deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 5/277:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/10$228
This FlightHub deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
Sun 4/267:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/12$246
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 5/177:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 2/12$248
This Trip.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 5/184:55 pm
YWG
-
ORD
1 stop23h 45m
WestJet
Deal found 2/12$270
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 5/189:05 pm
YWG
-
ORD
2 stops21h 49m
Multiple Airlines
Deal found 2/12$271
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:15 pm
ORD
-
YWG
1 stop23h 54m
Multiple Airlines
Thu 4/234:10 pm
YWG
-
ORD
2 stops24h 43m
Multiple Airlines
Deal found 2/12$272
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 5/179:05 pm
YWG
-
ORD
2 stops13h 39m
Multiple Airlines
Deal found 2/12$279
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:01 am
ORD
-
YWG
2 stops19h 39m
Multiple Airlines
Sun 4/267:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 2/11$287
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:16 pm
MDW
-
YWG
1 stop21h 53m
Multiple Airlines
Sun 3/87:30 am
YWG
-
MDW
1 stop14h 49m
Multiple Airlines
Deal found 2/10$289
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:05 am
ORD
-
YWG
1 stop10h 04m
Multiple Airlines
Mon 3/92:40 pm
YWG
-
ORD
2 stops15h 28m
Multiple Airlines
Deal found 2/10$292
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Fri 4/107:30 am
YWG
-
MDW
1 stop12h 37m
Multiple Airlines
Deal found 2/10$309
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:05 am
MDW
-
YWG
1 stop9h 04m
Multiple Airlines
Wed 3/188:05 pm
YWG
-
MDW
1 stop14h 00m
Multiple Airlines
Deal found 2/11$326

Find flight deals from Indiana to Winnipeg

Keep the following information in mind while searching for Indiana to Winnipeg flight deals. Data was last updated February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(oojo)

One-way from

$128
(Trip.com)
Provider with most accurate pricing for Indianapolis-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Indianapolis-Winnipeg flights.
Search Deals
From Indiana to Winnipeg
Search Deals
One-way flight from Indiana to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Indiana to Winnipeg that are best for you.

Fly from

Indiana

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/5

5:16 pm-3:09 pm

1 stop21h 53m

Winnipeg

Sun 3/8

7:30 am-10:19 pm

1 stop14h 49m

$289

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/6

6:05 am-3:09 pm

1 stop9h 04m

Winnipeg

Sun 3/8

7:30 am-7:47 pm

1 stop12h 17m

$289

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/6

5:05 am-3:09 pm

1 stop10h 04m

Winnipeg

Mon 3/9

2:40 pm-6:08 am

2 stops15h 28m

$292

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 4/8

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

Fri 4/10

7:30 am-8:07 pm

1 stop12h 37m

$309

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/8

5:15 am-12:40 am

2 stops19h 25m

Winnipeg

Fri 4/10

6:15 am-1:35 pm

1 stop7h 20m

$318

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 3/11

6:05 am-3:09 pm

1 stop9h 04m

Winnipeg

Wed 3/18

8:05 pm-10:05 am

1 stop14h 00m

$326

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 5/11

5:30 pm-5:25 pm

1 stop23h 55m

Winnipeg

Mon 6/1

7:00 am-4:40 pm

1 stop9h 40m

$328

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 3/11

8:55 pm-3:12 pm

1 stop18h 17m

Winnipeg

Wed 3/18

5:00 am-11:17 pm

2 stops18h 17m

$330

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 4/24

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Sun 4/26

10:30 pm-4:40 pm

2 stops18h 10m

$333

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/6

6:05 am-3:09 pm

1 stop9h 04m

Winnipeg

Mon 3/9

8:05 pm-1:02 pm

2 stops16h 57m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 39 results
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Best time to book a flight from Indiana to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Indiana with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Indiana to Winnipeg
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Indiana to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Indiana?

    Winnipeg (YWG) is the airport you will fly into if you book a flight from Indiana to Winnipeg. It is only a 4.6 mi journey from Winnipeg (YWG) to Winnipeg’s city center.

  • How long is the flight from Indiana to Winnipeg?

    A quick flight from Indiana to Winnipeg can take about 5h 19m. WestJet provides one of the quickest options available for as low as $487. The distance from Indiana to Winnipeg is about 936 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Indiana to Winnipeg?

    When deciding which route to take from Indiana to Winnipeg consider Chicago O'Hare Intl - Winnipeg, Chicago Midway - Winnipeg or Cincinnati Cinci./N. Kentucky - Winnipeg as they are the most popular.

  • Can I find deals for flights from Indiana to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Indiana to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Indiana to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Indiana to Winnipeg.

  • Can I find deals for business class flights from Indiana to Winnipeg?

    Yes. Cheapflights offers flight deals from Indiana to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Alternative routes for Indiana to Winnipeg

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Top airline flying from Indiana to Winnipeg

Discover the top airline that operate flights from Indiana to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$435Average$814FlexibilityNo cancel feeOn-timeN/A

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